Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature

doi:10.6023/cjoc202212008

Abstract

The thioesterification of esters with primary aliphatic thiols at room temperature was reported. The advantages of the method include transition-metal-free, mild conditions, good functional group tolerance, broad substrate scope and excellent chemoselectivity with respect to aliphatic alcohol ester and phenolic ester groups. This method was successfully applied to the synthesis of probenecid thioester and sequential bond activation.

Key words: thioesterification, esters, primary aliphatic thiols, transition-metal-free

Cite this article

Yijun Shi, Xinyue Sun, Han Cao, Fusheng Bie, Jie Ma, Zhe Liu, Xingshun Cong. Thioesterification of Esters with Primary Aliphatic Thiols at Room Temperature[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2499-2505.

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Entry	Base	Solvent	Yield^b/%
1	Na₂CO₃	THF	<5
2	K₂CO₃	THF	89
3	Cs₂CO₃	THF	73
4	NaHCO₃	THF	<5
5	K₃PO₄	THF	98
6	NaOAc	THF	<5
7	KOAc	THF	<5
8	KF	THF	<5
9	NaOH	THF	8
10	KOH	THF	45
11	LiOt-Bu	THF	88
12	NaOt-Bu	THF	10
13	KOt-Bu	THF	<5
14	Et₃N	THF	<5
15	DIPEA	THF	<5
16	DMAP	THF	<5
17	Pyridine	THF	<5
18	—	THF	<5
19	K₃PO₄	Toluene	<5
20	K₃PO₄	Dioxane	90
21	K₃PO₄	CH₃CN	82
22^c	K₃PO₄	THF	98
23^d	K₃PO₄	THF	98
24^e	K₃PO₄	THF	98
25^f	K₃PO₄	THF	73
26^g	K₃PO₄	THF	98
27^h	K₃PO₄	THF	88

Entry	Base	Solvent	Yield^b/%
1	Na₂CO₃	THF	<5
2	K₂CO₃	THF	89
3	Cs₂CO₃	THF	73
4	NaHCO₃	THF	<5
5	K₃PO₄	THF	98
6	NaOAc	THF	<5
7	KOAc	THF	<5
8	KF	THF	<5
9	NaOH	THF	8
10	KOH	THF	45
11	LiOt-Bu	THF	88
12	NaOt-Bu	THF	10
13	KOt-Bu	THF	<5
14	Et₃N	THF	<5
15	DIPEA	THF	<5
16	DMAP	THF	<5
17	Pyridine	THF	<5
18	—	THF	<5
19	K₃PO₄	Toluene	<5
20	K₃PO₄	Dioxane	90
21	K₃PO₄	CH₃CN	82
22^c	K₃PO₄	THF	98
23^d	K₃PO₄	THF	98
24^e	K₃PO₄	THF	98
25^f	K₃PO₄	THF	73
26^g	K₃PO₄	THF	98
27^h	K₃PO₄	THF	88

室温下酯与伯硫醇的硫酯化反应